CA3071779A1 - Carbamoyl phenylalaninol analogs and uses thereof - Google Patents
Carbamoyl phenylalaninol analogs and uses thereof Download PDFInfo
- Publication number
- CA3071779A1 CA3071779A1 CA3071779A CA3071779A CA3071779A1 CA 3071779 A1 CA3071779 A1 CA 3071779A1 CA 3071779 A CA3071779 A CA 3071779A CA 3071779 A CA3071779 A CA 3071779A CA 3071779 A1 CA3071779 A1 CA 3071779A1
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- Prior art keywords
- compound
- pharmaceutically acceptable
- acceptable salt
- formula
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- NJVZDURTFWBXAM-VIFPVBQESA-N [(2S)-1-hydroxy-3-phenylpropan-2-yl]urea Chemical class C(N)(=O)N[C@@H](CC1=CC=CC=C1)CO NJVZDURTFWBXAM-VIFPVBQESA-N 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 24
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- 239000000203 mixture Substances 0.000 claims description 40
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 208000035475 disorder Diseases 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000002552 dosage form Substances 0.000 claims description 15
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 13
- 206010041349 Somnolence Diseases 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- -1 cyano, hydroxy Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 3
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 108010020033 Vesicular Monoamine Transport Proteins Proteins 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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- OFLTYWJABWDXRC-RUMSDORHSA-N ethyl (e,4r)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpent-2-enoate Chemical compound CCOC(=O)\C=C\[C@H](NC(=O)OC(C)(C)C)CC1=CC=CC=C1 OFLTYWJABWDXRC-RUMSDORHSA-N 0.000 description 5
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- KGDTVHVCAZNGMH-GFCCVEGCSA-N tert-butyl N-[(2R)-1-phenyl-3-sulfamoyloxypropan-2-yl]carbamate Chemical compound S(N)(OC[C@@H](CC1=CC=CC=C1)NC(=O)OC(C)(C)C)(=O)=O KGDTVHVCAZNGMH-GFCCVEGCSA-N 0.000 description 5
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 4
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 4
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- KRXDPWRZLUHAAO-ZDUSSCGKSA-N tert-butyl N-[(2S)-5-amino-5-oxo-1-phenylpentan-2-yl]carbamate Chemical compound NC(CC[C@@H](CC1=CC=CC=C1)NC(OC(C)(C)C)=O)=O KRXDPWRZLUHAAO-ZDUSSCGKSA-N 0.000 description 4
- QNTMVPMDSVZSRV-GFCCVEGCSA-N tert-butyl n-[(2r)-1-carbamothioyloxy-3-phenylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](COC(N)=S)CC1=CC=CC=C1 QNTMVPMDSVZSRV-GFCCVEGCSA-N 0.000 description 4
- RGSVXQJPSWZXOP-UHFFFAOYSA-N 1-[1-(1-benzothiophen-2-yl)cyclohexyl]piperidine Chemical compound C1CCCCN1C1(C=2SC3=CC=CC=C3C=2)CCCCC1 RGSVXQJPSWZXOP-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
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- A—HUMAN NECESSITIES
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- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
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| US201762539088P | 2017-07-31 | 2017-07-31 | |
| US62/539,088 | 2017-07-31 | ||
| PCT/US2018/044465 WO2019027941A1 (en) | 2017-07-31 | 2018-07-31 | CARBAMOYL PHENYLALANINOL ANALOGUES AND USES THEREOF |
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| CA3071779A1 true CA3071779A1 (en) | 2019-02-07 |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11400065B2 (en) | 2019-03-01 | 2022-08-02 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11839597B2 (en) | 2016-07-22 | 2023-12-12 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2020108634A (ru) * | 2017-07-31 | 2021-09-02 | Джаз Фармасьютикалз Айрлэнд Лимитед | Аналоги карбамоилфенилаланинола и способы их применения |
| EP4531833A2 (en) * | 2022-06-03 | 2025-04-09 | Axsome Therapeutics | Carbamoyl phenylalaninol compounds as taar1 agonists |
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| SG11201903076QA (en) | 2016-10-06 | 2019-05-30 | Jazz Pharmaceuticals International Iii Ltd | Carbamoyl phenylalaninol compounds and uses therof |
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| US12226377B2 (en) | 2019-03-01 | 2025-02-18 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US12167992B2 (en) | 2019-03-01 | 2024-12-17 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US12167991B2 (en) | 2019-03-01 | 2024-12-17 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US11400065B2 (en) | 2019-03-01 | 2022-08-02 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US12303478B2 (en) | 2019-03-01 | 2025-05-20 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12295926B1 (en) | 2022-02-07 | 2025-05-13 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
Also Published As
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| US20210093603A1 (en) | 2021-04-01 |
| CN111094238A (zh) | 2020-05-01 |
| US11413264B2 (en) | 2022-08-16 |
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| WO2019027941A1 (en) | 2019-02-07 |
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| US20250017890A1 (en) | 2025-01-16 |
| KR20200045489A (ko) | 2020-05-04 |
| KR102643275B1 (ko) | 2024-03-04 |
| CN111094238B (zh) | 2023-06-09 |
| EP3661911A1 (en) | 2020-06-10 |
| SA520411187B1 (ar) | 2024-10-17 |
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